Water → Acryloyl-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

HRID 2383013Notes

Reaction equation

HRID 2383013 reaction equation
Cl.[CH:2]1([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C(Cl)Cl.C(N(CC)CC)C>[C:19]([C:8]1([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][NH:9]1)(=[O:22])[CH:20]=[CH2:21]

Participants

6

Reactant 3

HCID 962WaterHCID 13140Acryloyl chlorideHCID 675358401-Cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 70661750Acryloyl-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (800 mg) was dissolved in methylene chloride (12 mL), to which triethylamine (1.1 mL) and acryloyl chloride (0.28 mL) were then added under ice-cooling, followed by stirring under ice-cooling for 30 minutes and then stirring at room temperature for 14 hours. Water was added to the reaction liquid which was then extracted with chloroform. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated to obtain 2 acryloyl-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (856 mg).

Workup

  1. additionwere then added under ice-
  2. temperaturecooling
  3. temperaturecooling for 30 minutes
  4. stirringstirring at room temperature for 14 hours
  5. extractionwas then extracted with chloroform
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1222394dbe614dbab8e745e9ce1ab195
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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